Ketogenic and alcoholic beverage mixture containing non-racemic ethyl 3-hydroxybutyrate and/or 1,3 butanediol

ABSTRACT

A beverage can include D ethyl 3-hydroxybutyrate, D 1,3-butanediol, D Beta hydroxybutyrate salts, D Beta hydroxybutyrate/D 1,3-butanediol monoester, D ethyl hydroxybutyrate, hydroxybutyrate, and/or D hydroxybutyric acid of at least 0.5 percent by volume. The percentage of D ethyl 3-hydroxybutyrate, D 1,3-butanediol, D Beta hydroxybutyrate salts, D Beta hydroxybutyrate/D 1,3-butanediol monoester, D ethyl hydroxybutyrate, hydroxybutyrate, and D hydroxybutyric acid can be between 5 and 19 percent, or can be higher than 19 percent. The beverage can be improved by the incorporation of flavor from hops and/or from other ingredients.

TECHNICAL FIELD

This invention generally relates to beverages containing D ethyl3-hydroxybutyrate and/or D 1,3-butanediol and in particular to low carbbeers, beer-flavored beverages, sparkling water, spirits, and alcoholicbeverages, in place of or in addition to ethanol, which can facilitatethe initiation or maintenance of ketosis for persons trying to adhere toa ketogenic diet.

BACKGROUND

Ethyl 3-hydroxybutyrate, also known as Ethyl 3-hydroxybutanoate,3-Hydroxybutyric Acid Ethyl Ester is a well known flavor molecule and isan alcohol.

1,3-butanediol is also known as 1,3-butylene glycol, butane-1,3-diol, or1,3-dihydroxybutane. 1,3-butanediol is an organic compound, one of fourstable isomers of butanediol. It is also an alcohol. As shown in variousstudies, 1,3-butanediol can be safe for human consumption.

Ketosis is a fat-based metabolism, a state indicated by elevated levelsof ketones in the blood and in which a person's body produces ketonesfor fueling metabolism rather than primarily using glycogen to makeglucose. The ketogenic diet, which can initiate and maintain ketosis,was developed initially to treat pediatric refractory epilepsy. Theoriginal diet required ingesting calories primarily from fat, with aminimally sufficient amount of proteins to allow for growth and repair,and with a very restricted amount of carbohydrates. A typical diet wouldinclude a 4:1 ratio of fat to combined protein and carbohydrate (byweight). The ketogenic diet can allow one's body to consume fats forfuel rather than carbohydrates. Normally, the carbohydrates contained infood are stored as glycogen in the body and then, when needed, convertedinto glucose. Glucose is particularly important in fuelingbrain-function.

When a body lacks carbohydrates, the liver converts fat into fatty acidsand ketone bodies. The ketone bodies pass into the brain and replaceglucose as an energy source. An elevated level of ketone bodies in theblood, i.e. ketosis, has been shown to reduce the frequency of epilepticseizures. Ketosis may also improve brain-function when a person's bodycannot properly use glucose, such as in Alzheimer's patients and thosewith concussions or other brain damage.

In addition to improved brain-function, ketones can improve muscleperformance, such as in endurance athletes. This is because the body canonly store and convert about 100-minutes' worth of glycogen into usefulglucose during extreme and prolonged exercise, such as in bicycle racesand long-distance running. Athletes can train to extend their body'scapacity, but there are limits. Yet, with a second or alternative sourceof energy, from ketones, the body can continue to perform beyond theindividual's capacity to produce glucose. Further, studies have shownthat ketones can improve endurance performance by as much as twopercent.

SUMMARY

An aspect can include a beverage including a mixture of water and one ormore additives. The one or more additives are provided at aconcentration of at least 0.5 percent by volume. The one or moreadditives including at least one of the following: D ethyl3-hydroxybutyrate, D 1,3-butanediol, D beta hydroxybutyrate salts, Dbeta hydroxybutyrate/D 1,3-butanediol monoester, D ethylhydroxybutyrate, hydroxybutyrate (3-hydroxy-,3-ethoxy-1-methyl-3-oxopropyl ester), D hydroxybutyric acid, and (R, R)Butanoic acid, 3-hydroxy-, 3-ethoxy-1-methyl-3-oxopropyl ester.

An aspect can include a beverage. The beverage can include D ethyl3-hydroxybutyrate and/or D 1,3-butanediol. The percent by volume of Dethyl 3-hydroxybutyrate and/or D 1,3-butanediol can be of at least 0.5percent, greater than 5 percent, between 5 and 19 percent, and/or equalto or greater than 19 percent.

In some embodiments, the beverage can include flavor from hops includinghops essence. In other embodiments, the beverage can have fruit flavors.

Another aspect can include a process for making a beverage. The processcan include brewing a beer, halting fermentation, and adding D ethyl3-hydroxybutyrate and/or D 1,3-butanediol. The fermentation in thebrewing step can be halted before the percentage of alcohol by volumereaches 0.5 percent. The addition of D ethyl 3-hydroxybutyrate and/or D1,3-butanediol can increase the percentage of alcohol by volume to atleast 0.5 percent. The D form may be more bioavailable and provide agreater benefit to the consumer. However, the racemic form is currentlya low cost option, which may be more accessible to some consumers.

Yet another aspect can include a process for making a beverage. Theprocess can include fermenting a mixture and adding D ethyl3-hydroxybutyrate and/or D 1,3-butanediol to the mixture. The mixturecan include water and a fermentable food. Fermentation can achieve apercentage of alcohol by volume. D ethyl 3-hydroxybutyrate and/or D1,3-butanediol can be added to the mixture to increase the percentage ofalcohol by volume to at least 0.5 percent.

In some embodiments, the fermenting step can be halted before thepercentage of alcohol by volume reaches 0.5 percent. In otherembodiments, the fermenting step can achieve at least 0.5 percent ofethanol by volume and/or greater. In the latter embodiment, ethanol canbe extracted from the mixture to decrease the percentage of alcohol toless than 0.5 percent before adding D ethyl 3-hydroxybutyrate and/or1,3-butanediol to bring the percentage back up to at least 0.5 percent.

Other features and associated advantages will become apparent withreference to the following detailed description of specific embodimentsin connection with the accompanying drawings.

The free acid, D-beta-hydroxybutyrate and the salts thereof may be addedto alter and improve the flavor profile while at the same timeincreasing the net grams of D-beta-hydroxybutyrate without increasingthe alcohol content.

DESCRIPTION OF THE DRAWINGS

The following drawings form part of the present specification and areincluded to further demonstrate certain aspects of the presentinvention. The invention may be better understood by reference to one ormore of these drawings in combination with the detailed description ofspecific embodiments presented herein.

FIG. 1 is a line-angle formula of DL Ethyl 3-hydroxybutyrate;

FIG. 2 is a line-angle formula of D Ethyl 3-hydroxybutyrate;

FIG. 3 is a line-angle formula of 3-hydroxy-,3-ethoxy-1-methyl-3-oxopropyl ester; and

FIG. 4 is a graph illustrating blood ketone levels of racemic1,3-butanediol in comparison to chiral 1,3-butanediol.

DETAILED DESCRIPTION

A detailed explanation of the composition of matter and processaccording to preferred embodiments of the present invention aredescribed below.

D ethyl 3-hydroxybutyrate, and D 1,3-butanediol have each been shown tobe safe for human consumption. D ethyl 3-hydroxybutyrate, and D1,3-butanediol can each be converted into β-hydroxybutyrate and canserve as a substrate for brain metabolism. In addition, D ethyl3-hydroxybutyrate, and D 1,3-butanediol are hypoglycemic agents, meaningthey can reduce glucose levels in the blood. Moreover, when used, e.g.,as an alcohol in a beer, it can help initiate and/or maintain ketosis.

Beers, like many ethanol-based beverages, contain carbohydrates.Imbibing beer and/or ethanol-based beverages can prevent the initiationof ketosis and can destroy ketosis. Enjoying such beverages can bedifficult while trying to maintain or initiate ketosis. Those wishing toinitiate and/or maintain ketosis, whether it be for wellbeing, weightloss, health, lifestyle, and/or other reasons, can enjoy beer and/oralcoholic beverages while facilitating ketosis by drinking beer and/orbeverages that utilize D ethyl 3-hydroxybutyrate and/or D 1,3-butanediolin place of, or in addition to, ethanol. Moreover, unlike ethanol, theuse of D ethyl 3-hydroxybutyrate and/or D 1,3-butanediol can reduce theglycemic effects of ingesting the carbohydrates of the beer or beverage.

As used herein, the term “beverage” can relate to consumable liquidsincluding but not limited to water, carbonated water, naturally and/orartificially flavored waters, soft drinks, teas, juices, extractions,alcohol-containing beverages, and other known consumable liquids.Beverages can also include fermented beverages such as but not limitedto beers, ciders, wine, kombucha, spirits, hard soda, and other knownconsumable alcoholic beverages.

Embodiments can include a ketogenic friendly beer for those that pick aketogenic diet, which can entail maintaining ketone bodies in the bloodat levels, for example, above 0.5 mmol/L by restricting calories orcarbohydrate intake. Drinking beer that contains D ethyl3-hydroxybutyrate and/or D 1,3-butanediol can help maintain ketone bodylevels in the blood. Moreover, the D ethyl 3-hydroxybutyrate and/or D1,3-butanediol can help suppress glucose levels in the blood andcounteract the taking onboard of carbohydrates from in the beer. Forexample, a person may maintain a ketone body level of about 2.5 mmol/L.Drinking ethanol-based beer can result in a significant drop in theperson's ketone body level to, e.g., 0.2 mmol/L, the person can maintainand can even increase his or her ketone body level by drinking D ethyl3-hydroxybutyrate and/or D 1,3-butanediol beer. Depending on the ratioof D ethyl 3-hydroxybutyrate and/or D 1,3-butanediol-to-carbohydrate,the person's ketone body level can be lowered, though less severely thanfrom an ethanol beer, can be maintained, or can be increased.

In one embodiment, a “keto” beer or beverage, can facilitate ketosis. Itshould be understood that, as used herein, keto beer can refer to anybeverage in which the molecules and their precursors D ethyl3-hydroxybutyrate and/or D 1,3-butanediol are the primary alcoholingredient. In some embodiments, any of the following includingprecursors, can be utilized: D beta hydroxybutyrate salts, D betahydroxybutyrate, D 1,3-butanediol monoester, D ethyl hydroxybutyrate,hydroxybutyrate, D hydroxybutyric acid, and/or (R, R) Butanoic acid,3-hydroxy-, 3-ethoxy-1-methyl-3-oxopropyl ester. Each The ratio of Dethyl 3-hydroxybutyrate and/or D 1,3-butanediol to-total calorie of thebeer can be chosen such as to facilitate a ketogenic diet by providing aneutral or better than neutral effect on ketone body levels in adrinker's blood. For those who are not in ketosis, for example a ketonelevel of 0.0 to 0.5 mmol/L, a keto beer can facilitate initiation ofketosis. In some embodiments, a keto beer can further reduce glucoselevels that would otherwise be increased by the consumption of food,such as those in a meal.

Utilization of D ethyl 3-hydroxybutyrate and/or D 1,3-butanediol canhave other benefits. Its use can provide a temporary ketogenic effectthat can have benefits for weight loss and hunger suppression, as wellas improvement in brain-function and increased physical performance. Dethyl 3-hydroxybutyrate and/or D 1,3-butanediol can be utilized tocreate a beer or other alcoholic beverage that can be lower incarbohydrates than existing beers and/or cocktails, or it can be used tocreate beverages that have a net effect on how a body treats thosecarbohydrates. Due to the appetite suppression nature of ketone bodies,a ketogenic friendly beer can provide drinkers a full feeling andprevent them from over-drinking. Based at least in part on this effect,a keto beer can be safer than ethanol. Unlike traditional beer thatlowers inhibitions and can lead to further unregulated drinking, a ketobeer can provide a fuller and more content feeling at a lower quantityconsumed than with ethanol and can help reduce the desire to drink moreand become intoxicated. The beverage may be useful for recoveringalcoholics.

Some of those who imbibe alcoholic drinks can on occasion suffer fromso-called hangovers. Keto beer may reduce the severity or even eliminatehangovers and side effects common from ethanol based beer and drinkproducts.

A keto beer or wine can be made utilizing one or more of several steps.For example, in an embodiment, a beer can be made by providing mash,boiling the wort, adding hops, and then fermenting the wort into a beer,as known in the brewing arts. In the case of wine, grapes can be crushedand allowed to ferment. Ethanol from the fermentation can be extractedand replaced with D ethyl 3-hydroxybutyrate and/or D 1,3-butanediol.Extraction can be performed by boiling off the ethanol, which has a lowboiling point of about 173° F. at sea level. Extraction can also beperformed by fractional, or freeze, distillation, vacuum distillation,reverse-osmosis, or other methods for producing dealcoholized the beer.The beer can be considered dealcoholized, or nonalcoholic, when theethanol content is less than 0.5 percent alcohol by volume. Thesubstitution step can include providing the same, more, or less D ethyl3-hydroxybutyrate and/or D 1,3-butanediol than the amount of extractedethanol. To improve flavor, several steps can be performed before orafter alcohol substitution, such as dry-hopping, flavor-masking agents,and/or flavoring agents.

Keto beer can be carbonated by injecting CO2. Carbonation from CO2injection, while common and often acceptable, can cause metallic or sourflavors in some beverages. To further improve the taste of the beer,carbonation can be performed alternatively through a secondfermentation. The beer can be carbonated with the addition of sugar andstarter yeast. Very little ethanol is produced in the first 24-72 hoursof this second fermentation but CO2 can be produced. The yeast can bespecifically chosen from cultures known to produce little alcohol orthat are alcohol intolerant.

In an embodiment, a keto beer can be brewed as described above. However,before the fermentation process achieves 0.5 percent alcohol by volume(ABV), fermentation can be halted. D ethyl 3-hydroxybutyrate and/or D1,3-butanediol can be added to the beer to achieve a desired ABVpercentage.

In an embodiment, the beverage is provided with an additive includingpreservatives, color additives, flavors and spices, flavor enhancers,emulsifiers, and stabilizers.

D Ethyl 3-hydroxybutyrate and/or D 1,3-butanediol can also beadvantageously utilized as spirits. For example, substantially pure Dethyl 3-hydroxybutyrate and/or D 1,3-butanediol, or a high-contentsolution, can be utilized for mixing cocktails. The high-contentsolution can include D ethyl 3-hydroxybutyrate and/or D 1,3-butanedioland water. The solution can be aged with wood and/or include flavoradditives. A benefit of such cocktails is that they can provide pleasantintoxicating effects while also providing health benefits of a ketogenicdiet, for example by counteracting the carbohydrates present in mostcocktail recipes and by maintaining ketosis. Such alcoholic beveragescan assist in weight loss, either directly or from appetite suppression.

In an embodiment, the beverage is provided with an adjunct includingsolid and liquid adjuncts commonly used in the brewing arts.

In an embodiment, the beverage is provided with an additive includingpreservatives, color additives, flavors and spices, flavor enhancers,emulsifiers, and stabilizers.

In an embodiment, the beverage is provided as a low carbohydrate andeven a zero carbohydrate beverage. In one example, a low carbohydratebeverage can include beverages having a carbohydrate total of less than10 g per serving. All natural low calorie sweeteners such as Xylitol,Erythritol, monk fruit, and/or stevia and artificial sweeteners such assucrose, sucralose, acesulfame potassium, aspartame, saccharin can beutilized at a suitable concentration typical in beverage formulation.The beverage can be formulated as a low calorie beverage, such as abeverage having less than 100 calories per serving.

The term “additive”, as used herein can include D ethyl3-hydroxybutyrate, D 1,3-butanediol, D beta hydroxybutyrate salts, Dbeta hydroxybutyrate, D 1,3-butanediol monoester, D ethylhydroxybutyrate, hydroxybutyrate (3-hydroxy-,3-ethoxy-1-methyl-3-oxopropyl ester), D hydroxybutyric acid, and (R, R)Butanoic acid, 3-hydroxy-, 3-ethoxy-1-methyl-3-oxopropyl ester. The oneor more additives can be added in combination to provide a desirable andpalatable flavor profile to the beverage while avoiding potentialastringent or unpalatable flavors if provided individually. Further, itis known that pH balance and excessive salt intake are a result ofover-ingestion of certain therapeutic compounds. Mixing the moleculeslisted herein may promote a healthy pH balance and salt intakepost-ingestion.

When provided as an additive to a beverage, additive may, whetherindividually or in combination, provides an intoxicating effect to theconsumer without the unfavorable side-effects of ethanol intoxication.Further, each molecule has been shown to promote, induce, sustain,and/or regulate ketosis which has been shown to have a number ofdesirable benefits.

Flavoring agents can include, natural flavoring substances,nature-identical flavoring substances, artificial flavoring substances,diacetyl, acetylpropionyl, acetoin, isoamyl acetate, benzaldehyde,cinnamaldehyde, ethyl propionate, methyl anthranilate, limonene, ethyldecadienoate, allyl hexanoate, ethyl maltol, ethylvannillin, methylsalicylate, manzate, glutamic acid, glycine salts, guanylic acid,inosinic acid, acetic acid, malic acid, citric acid, ascorbic acid,fumaric acid, and lactic acid. Coloring agents can be added to provide afavorable color to the beverage mixture.

In some embodiments, the beverage is provided in a single-servingcontainer for consumer use. Alternatively, the beverage is provided in amulti-serving container such as a keg.

As one skilled in the art will appreciate, embodiments of the presentinvention may be embodied as, among other things, a composition ofmatter and a method for making compositions of matter. Other embodimentsare within the scope of the following claims.

1.-20. (canceled)
 21. A method of increasing ketone bodies exposure in asubject in need thereof, the method comprising administering a beveragecomprising water and at least 0.5 percent by volume enantiomericallyenriched 1,3-butanediol; the beverage further optionally comprising oneor more additives selected from the group consisting of D ethyl3-hydroxybutyrate; D beta hydroxybutyrate salts; D beta hydroxybutyrate,D 1,3-butanediol monoester; 3-hydroxy-, 3-ethoxy-1-methyl-3-oxopropylester; D hydroxybutyric acid; ethanol; and combinations thereof; whereinthe 1,3-butanediol is enriched with D-1,3-butanediol; and wherein theblood levels of ketone bodies is increased above 0.5 mmol/L.
 22. Themethod of claim 1, wherein the 1,3-butanediol is substantially pureD-1,3-butanediol.
 23. The method of claim 1, wherein the beveragefurther comprises a substrate.
 24. The method of claim 3, wherein thebeverage wherein the substrate comprises one or more flavoring agents.25. The method of claim 1, wherein the 1,3-butanediol is present at aconcentration of greater than 5 percent by volume.
 26. The method ofclaim 1, wherein the 1,3-butanediol is present at a concentration ofgreater than 19 percent by volume.
 27. The method of claim 1, whereinthe one or more additives are each partially or fully racemic.
 28. Themethod of claim 1, wherein the beverage is fermented.
 29. The method ofclaim 1, wherein the ethanol is not optional and is present at aconcentration of less than 0.5 percent by volume.
 30. The method ofclaim 1, wherein the beverage is carbonated.
 31. The method of claim 1,wherein the beverage comprises less than 10 g of carbohydrates perserving.
 32. A method of maintaining ketone bodies exposure in a subjectin need thereof, the method comprising administering a beveragecomprising water and at least 0.5 percent by volume enantiomericallyenriched 1,3-butanediol; the beverage further optionally comprising oneor more additives selected from the group consisting of D ethyl3-hydroxybutyrate; D beta hydroxybutyrate salts; D beta hydroxybutyrate,D 1,3-butanediol monoester; 3-hydroxy-, 3-ethoxy-1-methyl-3-oxopropylester; D hydroxybutyric acid; ethanol; and combinations thereof; whereinthe 1,3-butanediol is enriched with D-1,3-butanediol; and wherein theblood levels of ketone bodies is maintained above 0.5 mmol/L.
 33. Themethod of claim 12, wherein the 1,3-butanediol is substantially pureD-1,3-butanediol.
 34. The method of claim 12, wherein the beveragefurther comprises a substrate.
 35. The method of claim 14, wherein thebeverage wherein the substrate comprises one or more flavoring agents.36. The method of claim 12, wherein the 1,3-butanediol is present at aconcentration of greater than 5 percent by volume.
 37. The method ofclaim 12, wherein the 1,3-butanediol is present at a concentration ofgreater than 19 percent by volume.
 38. The method of claim 12, whereinthe one or more additives are each partially or fully racemic.
 39. Themethod of claim 12, wherein the beverage is carbonated.
 40. The methodof claim 1, wherein the beverage comprises less than 10 g ofcarbohydrates per serving.